Light-emitting device, electronic apparatus including the same, and organometallic compound

Abstract

A light-emitting device including a first electrode, a second electrode facing the first electrode, and an interlayer arranged between the first electrode and the second electrode including an emission layer. The interlayer includes an organometallic compound represented by Formula 1 and satisfying Condition 1:a minimum value of interior angles of an imaginary triangle including three atoms Y1 to Y3 as vertexes in the organometallic compound is less than 39°. Detailed descriptions of Formula 1 and Condition 1 are provided herein.

What is claimed is: 
     
         1 . A light-emitting device comprising:
 a first electrode;   a second electrode facing the first electrode; and   an interlayer arranged between the first electrode and the second electrode and comprising an emission layer,   wherein the interlayer comprises an organometallic compound represented by Formula 1 and satisfying Condition 1   
       
         
           
           
               
               
           
         
         wherein, in Formula 1, 
         M is platinum, palladium, gold, silver, nickel, or copper, 
         T 1  to T 4  are each independently a single bond, oxygen, or sulfur, 
         X 1  to X 4  are each independently carbon or nitrogen, 
         ring CY 2  to ring CY 4  are each independently a C 5 -C 60  carbocyclic group or a C 1 -C 60  heterocyclic group, 
         L 2  to L 4  are each independently a single bond, O, N(Z 1 ), or C(Z 1 )(Z 2 ), 
         b 2  and b 4  are each independently an integer from 0 to 2, 
         when b 2  is 0, (L 2 ) b2  is not present, and when b 4  is 0, (L 4 ) b4  is not present, 
         Z 1 , Z 2 , R 11  to R 13 , and R 2  to R 4  are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60  alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60  alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60  alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60  alkoxy group unsubstituted or substituted with at least one R 10a , a C 5 -C 60  carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60  heterocyclic group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ), 
         adjacent two of R 11  to R 13  are optionally bonded to each other to form a C 5 -C 60  carbocyclic group or a C 1 -C 60  heterocyclic group, 
         a2 to a4 are each independently an integer from 1 to 30, 
         a group represented by   is a single bond or a double bond, 
         R 10a  is deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; 
         a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, or a C 1 -C 60  alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 5 -C 60  carbocyclic group, a C 1 -C 60  heterocyclic group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 7 -C 60  aryl alkyl group, a C 2 -C 60  heteroaryl alkyl group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or a combination thereof; 
         a C 5 -C 60  carbocyclic group, a C 1 -C 60  heterocyclic group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 7 -C 60  aryl alkyl group, or a C 2 -C 60  heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, a C 1 -C 60  alkoxy group, a C 5 -C 60  carbocyclic group, a C 1 -C 60  heterocyclic group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 7 -C 60  aryl alkyl group, a C 2 -C 60  heteroaryl alkyl group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or a combination thereof; or 
         —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), 
         Q 1  to Q 3 , Q 11  to Q 13 , Q 21  to Q 23 , and Q 31  to Q 33  are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; or 
         a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, a C 1 -C 60  alkoxy group, a C 5 -C 60  carbocyclic group, a C 1 -C 60  heterocyclic group, a C 7 -C 60  aryl alkyl group, or a C 2 -C 60  heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60  alkyl group, a C 1 -C 60  alkoxy group, a phenyl group, a biphenyl group, or any combination thereof, 
         Condition 1 
         a minimum value of interior angles of an imaginary triangle including three atoms Y 1  to Y 3  as vertexes in the organometallic compound is less than 39°, 
         wherein, in Formula 1 and Condition 1, 
         a plane including 3 atoms, excluding an atom farthest from M among 4 atoms of i) T 1  or X 1  when T 1  is a single bond, ii) T 2  or X 2  when T 2  is a single bond, iii) T 3  or X 3  when T 3  is a single bond, and iv) T 4  or X 4  when T 4  is a single bond is defined as a first plane, 
         the first plane includes an x axis, which is an imaginary straight line including M and L 3 , and a y axis, which is an imaginary straight line including M and perpendicular to the x axis, wherein the x axis includes a positive direction directed from M towards L 3  and a negative direction directed from L 3  towards M, 
         an atom farthest from the first plane is defined as Y 1 , 
         among atoms included in a moiety represented by 
       
       
         
           
           
               
               
           
         
       
       an atom farthest from the y axis in the positive direction of the x axis is defined as Y 2 ,
 an atom farthest from the y axis in the negative direction of the x axis is defined as Y 3 , 
 * 1  indicates a binding site to T 3  in Formula 1, 
 * 2  indicates a binding site to T 4  in Formula 1, 
 * 3  indicates a binding site to (L 2 ) b2  in Formula 1, and 
 * 4  indicates a binding site to (L 4 ) b4  in Formula 1. 
 
     
     
         2 . The light-emitting device of  claim 1 , wherein the emission layer comprises the organometallic compound. 
     
     
         3 . The light-emitting device of  claim 1 , wherein the emission layer emits blue light. 
     
     
         4 . The light-emitting device of  claim 1 , wherein the interlayer further comprises a first compound comprising an azine group with at least one nitrogen atom. 
     
     
         5 . The light-emitting device of  claim 1 , wherein the interlayer further comprises a second compound comprising at least one carbazole group. 
     
     
         6 . The light-emitting device of  claim 5 , wherein an energy level of a lowest triplet excited state of the second compound is 2.8 electronvolts or greater. 
     
     
         7 . The light-emitting device of  claim 1 , wherein the interlayer further comprises a third compound comprising a polycyclic group in which at least 3 single rings are condensed. 
     
     
         8 . The light-emitting device of  claim 7 , wherein an energy difference between a lowest singlet excited state and a lowest triplet excited state of the third compound is less than 0.3 electronvolts. 
     
     
         9 . An electronic apparatus comprising the light-emitting device of  claim 1 . 
     
     
         10 . An organometallic compound represented by Formula 1 and satisfying Condition 1: 
       
         
           
           
               
               
           
         
         wherein, in Formula 1, 
         M is platinum), palladium, gold, silver, nickel, or copper, 
         T 1  to T 4  are each independently a single bond, oxygen, or sulfur, 
         X 1  to X 4  are each independently carbon or nitrogen, 
         ring CY 2  to ring CY 4  are each independently a C 5 -C 60  carbocyclic group or a C 1 -C 60  heterocyclic group, 
         L 2  to L 4  are each independently a single bond, O, N(Z 1 ), or C(Z 1 )(Z 2 ), 
         b 2  and b 4  are each independently an integer from 0 to 2, 
         when b 2  is 0, (L 2 ) b2  is not present, and when b 4  is 0, (L 4 ) b4  is not present, 
         Z 1 , Z 2 , R 11  to R 13 , and R 2  to R 4  are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60  alkyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60  alkenyl group unsubstituted or substituted with at least one R 10a , a C 2 -C 60  alkynyl group unsubstituted or substituted with at least one R 10a , a C 1 -C 60  alkoxy group unsubstituted or substituted with at least one R 10a , a C 5 -C 60  carbocyclic group unsubstituted or substituted with at least one R 10a , a C 1 -C 60  heterocyclic group unsubstituted or substituted with at least one R 10a , —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), or —P(═O)(Q 1 )(Q 2 ), 
         adjacent two of R 11  to R 13  are optionally bonded to each other to form a C 5 -C 60  carbocyclic group or a C 1 -C 60  heterocyclic group, 
         a2 to a4 are each independently an integer from 1 to 30, 
         a group represented by   is a single bond or a double bond, 
         R 10a  is deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; 
         a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, or a C 1 -C 60  alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 5 -C 60  carbocyclic group, a C 1 -C 60  heterocyclic group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 7 -C 60  aryl alkyl group, a C 2 -C 60  heteroaryl alkyl group, —Si(Q 11 )(Q 12 )(Q 13 ), —N(Q 11 )(Q 12 ), —B(Q 11 )(Q 12 ), —C(═O)(Q 11 ), —S(═O) 2 (Q 11 ), —P(═O)(Q 11 )(Q 12 ), or a combination thereof; 
         a C 5 -C 60  carbocyclic group, a C 1 -C 60  heterocyclic group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 7 -C 60  aryl alkyl group, or a C 2 -C 60  heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, a C 1 -C 60  alkoxy group, a C 5 -C 60  carbocyclic group, a C 1 -C 60  heterocyclic group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 7 -C 60  aryl alkyl group, a C 2 -C 60  heteroaryl alkyl group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), —P(═O)(Q 21 )(Q 22 ), or a combination thereof; or 
         —Si(Q 31 )(Q 32 )(Q 33 ), —N(Q 31 )(Q 32 ), —B(Q 31 )(Q 32 ), —C(═O)(Q 31 ), —S(═O) 2 (Q 31 ), or —P(═O)(Q 31 )(Q 32 ), 
         Q 1  to Q 3 , Q 11  to Q 13 , Q 21  to Q 23 , and Q 31  to Q 33  are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; or 
         a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, a C 1 -C 60  alkoxy group, a C 5 -C 60  carbocyclic group, a C 1 -C 60  heterocyclic group, a C 7 -C 60  aryl alkyl group, or a C 2 -C 60  heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C 1 -C 60  alkyl group, a C 1 -C 60  alkoxy group, a phenyl group, a biphenyl group, or any combination thereof, 
         Condition 1 
         a minimum value of interior angles of an imaginary triangle including three atoms Y 1  to Y 3  as vertexes in the organometallic compound is less than 39°, 
         wherein, in Formula 1 and Condition 1, 
         a plane including 3 atoms, excluding an atom farthest from M among 4 atoms of i) T 1  or X 1  when T 1  is a single bond, ii) T 2  or X 2  when T 2  is a single bond, iii) T 3  or X 3  when T 3  is a single bond, and iv) T 4  or X 4  when T 4  is a single bond is defined as a first plane, 
         the first plane includes an x axis, which is an imaginary straight line including M and L 3 , and a y axis, which is an imaginary straight line including M and perpendicular to the x axis, wherein the x axis includes a positive direction directed from M towards L 3  and a negative direction directed from L 3  towards M, 
         an atom farthest from the first plane is defined as Y 1 , 
         among atoms included in a moiety represented by 
       
       
         
           
           
               
               
           
         
       
       an atom farthest from the y axis in the positive direction of the x axis is defined as Y 2 ,
 an atom farthest from the y axis in the negative direction of the x axis is defined as Y 3 , 
 * 1  indicates a binding site to T 3  in Formula 1, 
 * 2  indicates a binding site to T 4  in Formula 1, 
 * 3  indicates a binding site to (L 2 ) b2  in Formula 1, and 
 * 4  indicates a binding site to (L 4 ) b4  in Formula 1. 
 
     
     
         11 . The organometallic compound of  claim 10 , wherein the minimum value of the interior angles of the imaginary triangle including three atoms Y 1  to Y 3  as vertexes in the organometallic compound is less than 37°. 
     
     
         12 . The organometallic compound of  claim 10 , wherein the organometallic compound further satisfies Condition 2:
 Condition 2   a minimum value of side lengths of the imaginary triangle including three atoms Y 1  to Y 3  as vertexes in the organometallic compound is 8 angstroms or greater, and   in Condition 2, atoms Y 1  to Y 3  are as defined in Condition 1.   
     
     
         13 . The organometallic compound of  claim 10 , wherein a minimum value of side lengths of the imaginary triangle including three atoms Y 1  to Y 3  as vertexes in the organometallic compound is 8.5 angstroms or greater. 
     
     
         14 . The organometallic compound of  claim 10 , wherein a distance between Y 1  and Y 2  or a distance between Y 1  and Y 3  has a minimum value of the side lengths of the imaginary triangle. 
     
     
         15 . The organometallic compound of  claim 10 , wherein <Y 1 Y 2 Y 3  or <Y 2 Y 3 Y 1  has a minimum value of the interior angles of the imaginary triangle. 
     
     
         16 . The organometallic compound of  claim 10 , wherein M in Formula 1 is platinum. 
     
     
         17 . The organometallic compound of  claim 10 , wherein Y 1  to Y 3  are each independently hydrogen or deuterium. 
     
     
         18 . The organometallic compound of  claim 10 , wherein a group represented by 
       
         
           
           
               
               
           
         
       
       in Formula 1 is a group represented by any one of Formulae CY1-1 to CY1-4: 
       
         
           
           
               
               
           
         
         wherein, in Formulae CY1-1 to CY1-4, 
         X 1  is as described in connection with Formula 1, 
         X 11  is N, C(H), C(D), or C(E 11 ), 
         X 12  is N, C(H), C(D), or C(E 12 ), 
         X 13  is O, S, N(E 13 ), or C(E 13 )(E 14 ), 
         D is deuterium, 
         R 1a , R 11a , and R 11f  are each as described in connection with R 10a , 
         R 12a  is as described in connection with R 12 , 
         R 13a  is as described in connection with R 13 , 
         R 11b , R 11c , R 11d , R 11e , and E 11  to E 14  are each independently deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C 1 -C 60  alkyl group, a C 2 -C 60  alkenyl group, a C 2 -C 60  alkynyl group, a C 1 -C 60  alkoxy group, a C 5 -C 60  carbocyclic group, a C 1 -C 60  heterocyclic group, a C 6 -C 60  aryloxy group, a C 6 -C 60  arylthio group, a C 7 -C 60  aryl alkyl group, a C 2 -C 60  heteroaryl alkyl group, —Si(Q 21 )(Q 22 )(Q 23 ), —N(Q 21 )(Q 22 ), —B(Q 21 )(Q 22 ), —C(═O)(Q 21 ), —S(═O) 2 (Q 21 ), or —P(═O)(Q 21 )(Q 22 ), 
         R 1a , R 11a  to R 11f , R 12a , and R 13a  are not bonded to each other, 
         ring CY 11  to ring CY 16  are each independently a C 5 -C 10  mono-carbocyclic group or a C 1 -C 10  mono-heterocyclic group, 
         e3 is an integer from 0 to 3, 
         e4 is an integer from 0 to 4, 
         a11 to a16 are each independently an integer from 0 to 5, and 
         * indicates to a binding site to T 1  in Formula 1, and *′ indicates a binding site to (L 4 ) b4  in Formula 1. 
       
     
     
         19 . The organometallic compound of  claim 10 , wherein the organometallic compound includes:
 a substituted or unsubstituted terphenyl group;   a substituted or unsubstituted 9-membered ring; or   any combination thereof, and   a substituent of each of the substituted 9-membered ring and the substituted terphenyl group includes   deuterium (—D), a C 1 -C 60  alkyl group, a phenyl group, or a triphenylsilyl group; or   a C 1 -C 60  alkyl group or a phenyl group, each substituted with deuterium, a C 1 -C 60  alkyl group, a phenyl group, a triphenylsilyl group, or any combination thereof.   
     
     
         20 . The organometallic compound of  claim 10 , wherein the organometallic compound emits blue light.